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What product is formed when (R)-2-chloropentane reacts with hydroxide ion in an SN2 reaction?

What product is formed when (R)-2-chloropentane reacts with hydroxide ion in an SN2 reaction?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### Topic: SN2 Reactions **Question:** What product is formed when (R)-2-chloropentane reacts with hydroxide ion in an SN2 reaction? **Answer Input Field:** ```plaintext [ ] ``` *(This field is for students to enter their answers in an interactive format on the website.)* --- **Explanation:** In an SN2 reaction, a nucleophile attacks the carbon atom that is bonded to a leaving group. Here, the hydroxide ion (OH-) serves as the nucleophile, and the chloride ion (Cl-) is the leaving group. The reaction proceeds with inversion of configuration at the carbon center, so (R)-2-chloropentane will be converted to (S)-2-pentanol. ### SN2 Mechanism: 1. **Nucleophilic Attack:** The hydroxide ion attacks the carbon that is attached to the chlorine atom from the opposite side. 2. **Transition State:** A transition state forms where the carbon is partially bonded to both the chlorine and the hydroxide ion. 3. **Leaving Group Departure:** The chloride ion leaves, resulting in an inversion of the stereochemistry of the carbon center. ### Product: **(S)-2-pentanol** This inversion happens due to the backside attack mechanism characteristic of SN2 reactions, leading to a change in spatial configuration from (R) to (S).
Transcribed Image Text:### Topic: SN2 Reactions **Question:** What product is formed when (R)-2-chloropentane reacts with hydroxide ion in an SN2 reaction? **Answer Input Field:** ```plaintext [ ] ``` *(This field is for students to enter their answers in an interactive format on the website.)* --- **Explanation:** In an SN2 reaction, a nucleophile attacks the carbon atom that is bonded to a leaving group. Here, the hydroxide ion (OH-) serves as the nucleophile, and the chloride ion (Cl-) is the leaving group. The reaction proceeds with inversion of configuration at the carbon center, so (R)-2-chloropentane will be converted to (S)-2-pentanol. ### SN2 Mechanism: 1. **Nucleophilic Attack:** The hydroxide ion attacks the carbon that is attached to the chlorine atom from the opposite side. 2. **Transition State:** A transition state forms where the carbon is partially bonded to both the chlorine and the hydroxide ion. 3. **Leaving Group Departure:** The chloride ion leaves, resulting in an inversion of the stereochemistry of the carbon center. ### Product: **(S)-2-pentanol** This inversion happens due to the backside attack mechanism characteristic of SN2 reactions, leading to a change in spatial configuration from (R) to (S).
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